


The Lesson

by cmsprite79



Series: Dean's Education [1]
Category: Supernatural
Genre: Aftercare, Anal Gaping, BDSM, Bondage, Chastity, D/s, Deep Throating, Dom Castiel, Dom Sam, Dub-Con-ish, Established Relationship, M/M, Spitroasting, Submissive Dean, butt plug, face fucking
Language: English
Status: Completed
Published: 2015-09-04
Updated: 2015-09-04
Packaged: 2018-04-19 00:17:25
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,684
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4725617
Author URL: https://archiveofourown.org/users/cmsprite79/pseuds/cmsprite79
Summary: <blockquote class="userstuff">
              <p>Dean's mostly a good boy, but sometimes he needs to be taught a lesson by his two Doms.</p>
            </blockquote>





	The Lesson

**Author's Note:**

> The dub-con-ish tag is because Dean protests any further "lessons" from his dominant partners. Other than that, everything is consensual. :) Takes place in an amorphous time-frame/place but I like to imagine it's after the boys find the Men of Letters Bunker. Enjoy! Also, Kudos and comments keep me alive. Thx!

By 2 a.m. Dean had lost count of how many times and ways he had been penetrated. He let out a low groan of pain as a cock, Sammy’s by the shear girth and length of it, pushed back into his fucked-out asshole. By now his ass gaped like the Grand Canyon and he couldn’t figure out why Sam would even _want_ to put his dick in there any more, he was so loose! Something hot and spongy nudged at his cracked lips and he automatically opened them even though his jaw was so sore it felt like it was going to fall off. He moaned around the member as it pushed to the back of his throat and stayed there, cutting off his air. His throat contracted involuntarily and he heard a gasp of pleasure from Cas.  


Dean’s eyes were closed but he could tell the moment Sam and Cas’s eyes met over him by the way their rhythms suddenly synchronized. They pounded into him at both ends, in at the same time, out at the same time. Dean reached for his own over-sensitive cock that had valiantly half-risen for the occasion but his hand was smacked away. He mewled in displeasure.  


“Fuck! Cas,” gasped Sam. “He’s so fucking loose!”  


“I know,” rumbled Cas. “He was the last two times I fucked him.”  


“Can…barely get any…friction. Damn it!” Sam changed angles and rammed his dick into Dean’s abused prostate. Dean let out a wail that Cas’s cock soon cut off. Dean’s dick was now painfully hard against his pelvis and it was all he could do to stay on his sore hands and abraded knees. His limbs trembled with the effort and he cursed Cas for the millionth time that night for using his angel powers to keep both him and Sam hard. Spit dribbled from Dean’s open mouth, pooling on the bed’s comforter below, adding to the various stains already there. Dean felt lube and come pour from his ass every time Sam rammed home. He felt filthy, just a hole for his brother and their best friend to fuck into. He hoped when this was all over that they’d let him come and then give him a shower but he honestly did not know if he could hold himself up long enough.  


“Think…ugh…think he’s learned his lesson yet, Cas?” Sam grunted, his fingers leaving another set of bruises on Dean’s hip bones.  


“He’ll never learn his lesson, Sam,” answered Cas as he used Dean’s short hair as a handle to better position Dean’s mouth on his cock. “We just have to keep teaching him over and over and over!” Each “over” was punctuated by a particularly harsh thrust down Dean’s throat and Dean’s eyes widened in panic. His lips would not only be chapped but they’d probably be bruised, too. He reached for Cas’s thigh with one shaking hand to push him back but Castiel caught Dean’s wrist and twisted Dean’s arm behind his back. Dean let out a shout that was only partially muffled by Cas’s dick. He felt more than heard Sam’s laugh and Sam said, “Heh, he looks good like that. Shoulda tied him up again.”  


Cas made an agreeing noise and paused fucking Dean’s face to reach for something on the bedside table. Dean struggled as Cas handcuffed his hands behind him but Sam and Cas had him effectively spit-roasted between them. There was no way he could get away. “Better,” mused Sam and ran one appreciative hand down the length of Dean’s spine, over his cuffed wrists, and down to where they were joined. Dean tried to wriggle forward while Sam’s fingers traced over his tortured rim. “Don’t think the plug will fit him anymore, unfortunately.”  


“I’ll produce a larger one,” said Cas, panting at Dean’s anguished moan around his cock.  


“Good,” said Sam. “Are you close?”  


“Yeah.”  


“Me too.”  


_Thank fuck!_ Thought Dean. He just wanted this round to be over. He felt one of his brother’s meaty paws on his aching dick and nearly cried with relief. Sam’s thrusting became erratic and Cas kept holding Dean’s face down into his pubes so tightly that Dean thought he would soon pass out. But just as his vision started to gray, he felt the first twitches of Cas’s orgasm along his tongue and prepared himself to swallow what he knew was going to be a pretty generous load. Meanwhile, Sam pressed in as tight as he could and stilled, depositing probably the tenth load of come Dean had had up his ass since this all started at 9:30 last night. It practically burned inside Dean and he felt his own orgasm reaching its peak. His aching balls didn’t even produce sperm any more, just a dribble of precome. He came dry, dick so sensitive that he immediately tried to move away from Sam’s grip, but he couldn’t. The damn Sasquatch practically collapsed on top of him, sending Cas’s cock to the very depths of Dean’s throat. Cas shouted and came copiously into his chosen receptacle. Dean swallowed. It was ingrained into his reflexes now.  


He whined as both men pulled out of him. There was a slight popping sound and then something was being shoved deep into his gaping ass, a plug, twice the girth and length of the one that had been in his butt off and on since yesterday afternoon. He groaned at the heaviness and discomfort then groaned again as Sammy attached some straps between his legs and around his waist to keep the plug in place. “Cock cage?” Sammy asked over Dean’s head. He heard and felt Cas pass said cage over him to his brother. He couldn’t help himself wince as Sammy locked the silver metal cage around his tender dick and balls. Sam petted Dean’s ass when he was done and took the key Cas passed him to undo the handcuffs. Dean fell limply onto his side once the men were done with him.  


Cas stroked Dean’s face and thumbed his chapped lips. He produced a bottle of water from somewhere and propped Dean’s head up to help him drink.  


“I’ll go start the shower,” said Sam and got off the bed.  


“Great,” said Cas and caressed Dean’s head and throat as Dean suckled at the water bottle like an infant. “Such a good boy for us, Dean. But I don’t think you’ve quite learned your lesson yet.” Dean made a low sound of protest. Words were beyond him right now. Cas hushed him and took the water bottle away for a moment so he could kiss Dean’s sensitive mouth. When he pulled back, Dean managed to whisper, “No more, please? I…I _can’t_!”  


“Shh, yes you can,” said Cas and returned the water bottle to Dean’s lips. Dean moved his head away from it and into Cas’s shoulder.  


“Nooo! I learned my lesson, I _swear_!”  


Cas was silent for a minute and then asked, “All right, what’s the lesson then?”  


Dean’s mind had to process the question. What were they punishing him for? Oh yeah. “Gotta…gotta learn to share the remote control.”  


“Right, very good, Dean,” said Cas and smiled down at him. “I guess you have learned it, then.”  


Just then, Sam returned and announced that the shower was all set. He and Cas each took Dean under one arm and helped him off the bed. Dean moaned, gasped, or grunted in discomfort almost every step of the way. Sam and Cas chuckled. They had one weary-assed hunter on their hands! Dean stood under the spray of the shower, legs trembling, as Sam and Cas soaped him up and rinsed him down. Cas relayed Dean’s learning of his lesson to Sam. Sam’s eyebrows drew together and his mouth turned down at the corners.  


“Are you sure?” Sam asked, tweaking one of Dean’s nipples just to see Dean yelp and squirm.  


“Well…” Cas let the sentence hang.  


“Yes! Yes I freakin’ learned my lesson!” Dean practically yelled. Sam and Cas both laughed.  


“All right, all right, relax. You’ve learned your lesson,” said Sam and drew his brother in for a deep kiss. Dean groaned into Sam’s mouth. Cas’s hands squeezed the slick globes of Dean’s ass. When Sam pulled back he looked into Dean’s pupil-blown eyes with a mischievous smirk. “But,” he said, “who knows when you’ll need a reminder, huh? Or maybe we’ll have to teach you to share something else? The Impala, maybe?”  


“Nooo!” Dean whined and Cas gave him a dirty smack on one ass cheek.  


“Yes,” whispered Sam excitedly in Dean’s ear.  


“Sounds like Dean missed out on the basics of sharing in kindergarten,” observed Cas who now had his hands cupping Dean’s caged cock. Dean tried to squirm away from Cas touching his still sensitive manhood.  


“Nooo!” Dean practically sobbed and his legs started to go out from under him.  


“Yep, he’ll have lots of lessons to learn since we have to start at the beginning,” agreed Sam who caught most of Dean’s weight and helped him out of the shower. Cas followed and reached for towels since Sam’s hands were full. Once they were all dried, Sam carried Dean to the bedroom and laid him down on top of the covers. Dean felt a few wet spots under him but he couldn’t bring himself to care. He really couldn’t take another “lesson” tonight.  


“Even kindergartners get recess, though,” said Cas as he and Sam stared down at Dean.  


“Yeah. I guess we’ll have to let him rest a bit before the next lesson.” Cas helpfully peeled the covers from under Dean and replaced them over him, tucking him in gently. Dean was already half-asleep, plug and cock cage nearly forgotten in his exhaustion.  


“What method should we use next time?” Sam asked, tidying the room a bit since it had gotten disheveled in their marathon sex run.  


Dean’s eyes flew open at Castiel’s answer. “I’ve heard that using a cane along with some intense sensory deprivation can work wonders on naughty submissives.” Dean was so screwed!


End file.
